On-Demand Dissolution of Chemically Cross-Linked Hydrogels

Accounts of Chemical Research

Volumn 50, Issue 2, 2017, Pages 151-160

  Konieczynska, Marlena D ^a   Grinstaff, Mark W ^a  

^a BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMATERIAL; DISULFIDE; THIOL DERIVATIVE;

CHEMISTRY; CYCLOADDITION; HYDROGEL; SOLUBILITY;

BIOCOMPATIBLE MATERIALS; CYCLOADDITION REACTION; DISULFIDES; HYDROGELS; SOLUBILITY; SULFHYDRYL COMPOUNDS;

EID: 85013679039     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.6b00547     Document Type: Article

References (40)

1. Wichterle, O.; Lim, D. Hydrophilic Gels for Biological Use Nature 1960, 185 ( 4706 ) 117-118 10.1038/185117a0
2. Drury, J. L.; Mooney, D. J. Hydrogels for Tissue Engineering: Scaffold Design Variables and Applications Biomaterials 2003, 24 ( 24 ) 4337-4351 10.1016/S0142-9612(03)00340-5
3. Peppas, N. A.; Bures, P.; Leobandung, W.; Ichikawa, H. Hydrogels in Pharmaceutical Formulations Eur. J. Pharm. Biopharm. 2000, 50 ( 1 ) 27-46 10.1016/S0939-6411(00)00090-4
4. Caló, E.; Khutoryanskiy, V. V. Biomedical Applications of Hydrogels: A Review of Patents and Commercial Products Eur. Polym. J. 2015, 65, 252-267 10.1016/j.eurpolymj.2014.11.024
5. Kharkar, P. M.; Kiick, K. L.; Kloxin, A. M. Designing Degradable Hydrogels for Orthogonal Control of Cell Microenvironments Chem. Soc. Rev. 2013, 42 ( 17 ) 7335-7372 10.1039/C3CS60040H
6. Ehrbar, M.; Rizzi, S. C.; Schoenmakers, R. G.; San Miguel, B.; Hubbell, J. A.; Weber, F. E.; Lutolf, M. P. Biomolecular Hydrogels Formed and Degraded via Site-Specific Enzymatic Reactions Biomacromolecules 2007, 8 ( 10 ) 3000-3007 10.1021/bm070228f
7. Li, X.; Tsutsui, Y.; Matsunaga, T.; Shibayama, M.; Chung, U.; Sakai, T. Precise Control and Prediction of Hydrogel Degradation Behavior Macromolecules 2011, 44 ( 9 ) 3567-3571 10.1021/ma2004234
8. Nicodemus, G. D.; Bryant, S. J. Cell Encapsulation in Biodegradable Hydrogels for Tissue Engineering Applications Tissue Eng., Part B 2008, 14 ( 2 ) 149-165 10.1089/ten.teb.2007.0332
9. Larsson, R.; Pei, Z.; Ramström, O. Catalytic Self-Screening of Cholinesterase Substrates from a Dynamic Combinatorial Thioester Library Angew. Chem., Int. Ed. 2004, 43 ( 28 ) 3716-3718 10.1002/anie.200454165
10. Hupe, D. J.; Jencks, W. P. Nonlinear Structure-Reactivity Correlations. Acyl Transfer between Sulfur and Oxygen Nucleophiles J. Am. Chem. Soc. 1977, 99 ( 2 ) 451-464 10.1021/ja00444a023
11. Anumolu, S. S.; Menjoge, A. R.; Deshmukh, M.; Gerecke, D.; Stein, S.; Laskin, J.; Sinko, P. J. Doxycycline Hydrogels with Reversible Disulfide Cross-links for Dermal Wound Healing of Mustard Injuries Biomaterials 2011, 32 ( 4 ) 1204-1217 10.1016/j.biomaterials.2010.08.117
12. Wathier, M.; Johnson, C. S.; Kim, T.; Grinstaff, M. W. Hydrogels Formed by Multiple Peptide Ligation Reactions to Fasten Corneal Transplants Bioconjugate Chem. 2006, 17 ( 4 ) 873-876 10.1021/bc060060f
13. Hu, B.-H.; Su, J.; Messersmith, P. B. Hydrogels Cross-Linked by Native Chemical Ligation Biomacromolecules 2009, 10 ( 8 ) 2194-2200 10.1021/bm900366e
14. Ghobril, C.; Charoen, K.; Rodriguez, E. K.; Nazarian, A.; Grinstaff, M. W. A Dendritic Thioester Hydrogel Based on Thiol-Thioester Exchange as a Dissolvable Sealant System for Wound Closure Angew. Chem., Int. Ed. 2013, 52 ( 52 ) 14070-14074 10.1002/anie.201308007
15. Carlmark, A.; Hawker, C.; Hult, A.; Malkoch, M. New Methodologies in the Construction of Dendritic Materials Chem. Soc. Rev. 2009, 38 ( 2 ) 352-362 10.1039/B711745K
16. Wathier, M.; Johnson, M. S.; Carnahan, M. A.; Baer, C.; McCuen, B. W.; Kim, T.; Grinstaff, M. W. In Situ Polymerized Hydrogels for Repairing Scleral Incisions Used in Pars Plana Vitrectomy Procedures ChemMedChem 2006, 1 ( 8 ) 821-825 10.1002/cmdc.200600090
17. Konieczynska, M. D.; Villa-Camacho, J. C.; Ghobril, C.; Perez-Viloria, M.; Blessing, W. A.; Nazarian, A.; Rodriguez, E. K.; Grinstaff, M. W. A Hydrogel Sealant for the Treatment of Severe Hepatic and Aortic Trauma with a Dissolution Feature for Post-Emergent Care Mater. Horiz. 2017, 10.1039/C6MH00378H
18. Kauvar, D. S.; Lefering, R.; Wade, C. E. Impact of Hemorrhage on Trauma Outcome: An Overview of Epidemiology, Clinical Presentations, and Therapeutic Considerations J. Trauma: Inj., Infect., Crit. Care 2006, 60 ( 6 ) S3-S11 10.1097/01.ta.0000199961.02677.19
19. Kragh, J. F. J.; Littrel, M. L.; Jones, J. A.; Walters, T. J.; Baer, D. G.; Wade, C. E.; Holcomb, J. B. Battle Casualty Survival with Emergency Tourniquet Use to Stop Limb Bleeding J. Emerg. Med. 2011, 41 ( 6 ) 590-597 10.1016/j.jemermed.2009.07.022
20. Villa-Camacho, J. C.; Ghobril, C.; Anez-Bustillos, L.; Grinstaff, M. W.; Rodríguez, E. K.; Nazarian, A. The Efficacy of a Lysine-Based Dendritic Hydrogel Does Not Differ from Those of Commercially Available Tissue Sealants and Adhesives: An Ex Vivo Study BMC Musculoskeletal Disord. 2015, 16, 116 10.1186/s12891-015-0573-7
21. Johnson, E. C. B.; Kent, S. B. H. Insights into the Mechanism and Catalysis of the Native Chemical Ligation Reaction J. Am. Chem. Soc. 2006, 128 ( 20 ) 6640-6646 10.1021/ja058344i
22. Holcomb, J. B.; McClain, J. M.; Pusateri, A. E.; Beall, D.; Macaitis, J. M.; Harris, R. A.; MacPhee, M. J.; Hess, J. R. Fibrin Sealant Foam Sprayed Directly on Liver Injuries Decreases Blood Loss in Resuscitated Rats J. Trauma 2000, 49 ( 2 ) 246-250 10.1097/00005373-200008000-00010
23. Ferretti, L.; Qiu, X.; Villalta, J.; Lin, G. Efficacy of BloodSTOP iX, Surgicel, and Gelfoam in Rat Models of Active Bleeding from Partial Nephrectomy and Aortic Needle Injury Urology 2012, 80 ( 5 ) 1161.e1-1161.e6 10.1016/j.urology.2012.06.048
24. Konieczynska, M. D.; Villa-Camacho, J. C.; Ghobril, C.; Perez-Viloria, M.; Tevis, K. M.; Blessing, W. A.; Nazarian, A.; Rodriguez, E. K.; Grinstaff, M. W. On-Demand Dissolution of a Dendritic Hydrogel-Based Dressing for Second-Degree Burn Wounds through Thiol-Thioester Exchange Reaction Angew. Chem., Int. Ed. 2016, 55 ( 34 ) 9984-9987 10.1002/anie.201604827
25. Borman, H.; Maral, T.; Demirhan, B.; Haberal, M. Skin Flap Survival after Superficial and Deep Partial-Thickness Burn Injury Ann. Plast. Surg. 1999, 43 ( 5 ) 513-518 10.1097/00000637-199911000-00008
26. Barnea, Y.; Carmeli, Y.; Kuzmenko, B.; Gur, E.; Hammer-Munz, O.; Navon-Venezia, S. The Establishment of a Pseudomonas Aeruginosa-Infected Burn-Wound Sepsis Model and the Effect of Imipenem Treatment Ann. Plast. Surg. 2006, 56 ( 6 ) 674-679 10.1097/01.sap.0000203984.62284.7a
27. Houk, J.; Whitesides, G. M. Structure-Reactivity Relations for Thiol-Disulfide Interchange J. Am. Chem. Soc. 1987, 109 ( 22 ) 6825-6836 10.1021/ja00256a040
28. Gyarmati, B.; Némethy, Á.; Szilágyi, A. Reversible Disulphide Formation in Polymer Networks: A Versatile Functional Group from Synthesis to Applications Eur. Polym. J. 2013, 49 ( 6 ) 1268-1286 10.1016/j.eurpolymj.2013.03.001
29. Nair, D. P.; Podgórski, M.; Chatani, S.; Gong, T.; Xi, W.; Fenoli, C. R.; Bowman, C. N. The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry Chem. Mater. 2014, 26 ( 1 ) 724-744 10.1021/cm402180t
30. Friedman, M.; Cavins, J. F.; Wall, J. S. Relative Nucleophilic Reactivities of Amino Groups and Mercaptide Ions in Addition Reactions with A,β-Unsaturated Compounds1,2 J. Am. Chem. Soc. 1965, 87 ( 16 ) 3672-3682 10.1021/ja01094a025
31. Baldwin, A. D.; Kiick, K. L. Tunable Degradation of Maleimide-Thiol Adducts in Reducing Environments Bioconjugate Chem. 2011, 22 ( 10 ) 1946-1953 10.1021/bc200148v
32. Baldwin, A. D.; Kiick, K. L. Reversible Maleimide-thiol Adducts Yield Glutathione-Sensitive Poly(ethylene Glycol)-heparin Hydrogels Polym. Chem. 2013, 4 ( 1 ) 133-143 10.1039/C2PY20576A
33. Nie, T.; Akins, R. E., Jr.; Kiick, K. L. Production of Heparin-Containing Hydrogels for Modulating Cell Responses Acta Biomater. 2009, 5 ( 3 ) 865-875 10.1016/j.actbio.2008.12.004
34. Elbert, D. L.; Pratt, A. B.; Lutolf, M. P.; Halstenberg, S.; Hubbell, J. A. Protein Delivery from Materials Formed by Self-Selective Conjugate Addition Reactions J. Controlled Release 2001, 76 ( 1-2 ) 11-25 10.1016/S0168-3659(01)00398-4
35. Koehler, K. C.; Anseth, K. S.; Bowman, C. N. Diels-Alder Mediated Controlled Release from a Poly(ethylene Glycol) Based Hydrogel Biomacromolecules 2013, 14 ( 2 ) 538-547 10.1021/bm301789d
36. Nimmo, C. M.; Owen, S. C.; Shoichet, M. S. Diels-Alder Click Cross-Linked Hyaluronic Acid Hydrogels for Tissue Engineering Biomacromolecules 2011, 12 ( 3 ) 824-830 10.1021/bm101446k
37. Tan, H.; Rubin, J. P.; Marra, K. G. Direct Synthesis of Biodegradable Polysaccharide Derivative Hydrogels Through Aqueous Diels-Alder Chemistry Macromol. Rapid Commun. 2011, 32 ( 12 ) 905-911 10.1002/marc.201100125
38. Sanyal, A. Diels-Alder Cycloaddition-Cycloreversion: A Powerful Combo in Materials Design Macromol. Chem. Phys. 2010, 211 ( 13 ) 1417-1425 10.1002/macp.201000108
39. Kirchhof, S.; Brandl, F. P.; Hammer, N.; Goepferich, A. M. Investigation of the Diels-Alder Reaction as a Cross-Linking Mechanism for Degradable Poly(ethylene Glycol) Based Hydrogels J. Mater. Chem. B 2013, 1 ( 37 ) 4855-4864 10.1039/c3tb20831a
40. Kirchhof, S.; Strasser, A.; Wittmann, H.-J.; Messmann, V.; Hammer, N.; Goepferich, A. M.; Brandl, F. P. New Insights into the Cross-Linking and Degradation Mechanism of Diels-Alder Hydrogels J. Mater. Chem. B 2015, 3 ( 3 ) 449-457 10.1039/C4TB01680G